EP1765463B1 - Compositions cosmetiques et procede a base d'un agent bronzant et d'acide ursolique encapsule dans un liposome - Google Patents

Compositions cosmetiques et procede a base d'un agent bronzant et d'acide ursolique encapsule dans un liposome Download PDF

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Publication number
EP1765463B1
EP1765463B1 EP05772127.6A EP05772127A EP1765463B1 EP 1765463 B1 EP1765463 B1 EP 1765463B1 EP 05772127 A EP05772127 A EP 05772127A EP 1765463 B1 EP1765463 B1 EP 1765463B1
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EP
European Patent Office
Prior art keywords
liposome
skin
ursolic acid
dha
tanning
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Not-in-force
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EP05772127.6A
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German (de)
English (en)
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EP1765463A2 (fr
EP1765463A4 (fr
Inventor
Paolo U. Giacomoni
Abul M. Manirazman
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EL Management LLC
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EL Management LLC
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Publication of EP1765463A4 publication Critical patent/EP1765463A4/fr
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/04—Preparations for care of the skin for chemically tanning the skin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/14—Liposomes; Vesicles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/63—Steroids; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/10—Dispersions; Emulsions
    • A61K9/127—Liposomes

Definitions

  • the present invention relates to skin care cosmetic compositions and methods.
  • the present invention relates to novel cosmetic compositions and methods comprising the novel combination of a tanning agent such as dihydroxy acetone (DHA) and liposome encapsulated ursolic acid.
  • a tanning agent such as dihydroxy acetone (DHA)
  • liposome encapsulated ursolic acid a tanning agent
  • a tan is often considered a sign of physical health and social success.
  • a tan can be achieved naturally by exposing one's skin to solar or artificial ultraviolet radiation, or by the use of self-tanning products.
  • a tan generated by exposure to ultraviolet radiation is undesirable because of the known adverse effects of prolonged exposure to such UV-A radiation.
  • DHA dihydroxy acetone
  • the present invention provides a composition for topical application to the skin to provide tanning comprising a liposome encapsulated ursolic acid, a tanning agent and a cosmetically acceptable carrier.
  • the present invention further provides a method of tanning comprising topically applying to the skin, a composition comprising a liposome encapsulated ursolic acid, dihydroxyacetone and a cosmetically acceptable carrier.
  • Ursolic acid is a nontoxic, naturally-occurring triterpenoid that is found in a variety of plants with medicinal properties. Studies have shown that ursolic acid has both antiinflammatory, antitumor and antiaging properties. See “ Pharmacology of Oleanonic Acid and Ursolic Acid,” Journal of Ethnopharmacology, 49, 57-58, 1995 . Ursolic acid, however, is difficult to solubilize. For example, ursolic acid dissolved in ethanol or other alcohols come out of solution when applied to cultured cells. Moreover, ursolic acid can exhibit poor penetration in human skin when incorporated into a common solvent. See “ Liposome-encapsulated ursolic acid increases in ceramides and collagen in human skin cells," by Dawn M.
  • ursolic acid is incorporated into vesicles that enhance the ability of ursolic acid in penetrating into the skin.
  • Liposomes are the smallest artificial vesicles of spherical shape that can be produced from natural non-toxic phospholipids and cholesterol. See “ What are Liposomes," Laboratory of Liposomal Research, November 18, 2003 . Liposomes have been used as vesicles for carrying a great variety of molecules, such as small drug molecules, proteins, nucleotides and plasmids. Liposomes are extremely versatile and due to the variability of their composition, they can be used for a large number of applications, including delivery of actives into the skin in cosmetic applications. It has been found that liposome based formulations do not disturb the integrity of the skin lipid bilayers and are not washed out while cleaning the skin.
  • URA liposome-encapsulated ursolic acid As a result of attempts to protect ursolic acid in vesicles, recent studies have shown that liposome-encapsulated ursolic acid (“URA liposome”) overcome the solubilizing difficulties discussed hereinabove. Moreover, URA liposomes have been shown to provide anti-aging benefits through increase of ceramide and collagen content in human skin cells, as well as antiinflammatory and antitumor properties. See “ Liposome-encapsulated ursolic acid increases in ceramides and collagen in human skin cells," by Dawn M. Both, Karina Goodtzova, Daniel B. Yarosh, and David A. Brown, Arch Dermatol Res, 2002, 293: 569-575 .
  • the present invention is predicated on the surprising observation that dihydroxyacetone ("DHA") in combination with at least one URA liposome provides an unexpectedly rapid and relatively natural-looking darkening/tanning of human skin. While not wishing to be bound by any theories, it is believed that because the URA liposome is better able to penetrate the skin, the URA liposome opens a pathway for the DHA to also better penetrate the skin to provide a more pronounced and rapid darkening/tanning of the skin. Specifically, as has been discussed hereinabove, it is believed that URA is difficult to solubilize for penetration into the skin, and therefore the liposomes provide the vesicle for carrying the URA into the skin. Upon opening a pathway into the skin, the DHA of the inventive composition comprising the combination of DHA and URA liposomes can readily follow the pathway into the skin.
  • DHA dihydroxyacetone
  • Liposomes of the present invention can be formed from a variety of phospholipids, such as cholesterol, stearylamine, or phosphatidylcholines. Lipids from egg yolks or soybeans can also be used to make liposomes. Conventional liposome preparation methods include a number of steps in which multi- or the bilayer-forming components (phospholipids or mixtures of phospholipids with other lipids e.g. cholesterol) are dissolved in a volatile organic solvent or solvent mixture in a flask followed by evaporation of the solvent under conditions such as temperature and pressure which will prevent phase separation.
  • multi- or the bilayer-forming components phospholipids or mixtures of phospholipids with other lipids e.g. cholesterol
  • a dry lipid mixture Upon solvent removal, a dry lipid mixture, usually in the form of a film deposit on the walls of the reactor, is hydrated with an aqueous medium which may contain dissolved buffers, salts, conditioning agents and an active substance to be entrapped. Liposomes will form in the hydration step whereby a proportion of the aqueous medium becomes encapsulated in the liposomes.
  • the hydration can be performed with or without energizing the solution by means of stirring, sonication or microfluidisation with subsequent extrusion through one or more polycarbonate filters.
  • the free non-encapsulated active substance can be separated for recovery and the product is filtered, sterilized, optionally lyophilized, and packed.
  • liposomes Other methods of making liposomes involve injection of an organic solutions of lipids into an aqueous medium with continuous removal of solvent, use of spray drying, lyophilization, microemulsification and microfluidization. See U.S. Pat. No. 4,529,561 and U.S. Pat. No. 4,572,425 .
  • ursolic acid for incorporation into the liposome, can be in an isolated form or provided as a pure/semi-pure form of an extract. More specifically, ursolic acid may be derived from a plant, as for example from a plant part or as a solvent extract. Ursolic acid may be found in a variety of plants, including but not limited to, Calluna vulgaris (Ericaceae), Eribotrya japonica (Rosaceae), Eucalyptus hybrid (Myrtaceae), Melaleuca leucadendron L. (Myrtaceae), Glechoma hederacea L.
  • the concentrations of the active ursolic acid may vary from source to source, so as a guideline, it is recommended to use the amount of extract that would provide an equivalent concentration of isolated ursolic acid in a range of from 0.0001 to 5%.
  • ursolic acid is the principle active component in achieving tanning
  • additional components although not necessarily very effective on their own, may be present in the plant extracts that can have some contributory activity.
  • the liposome encapsulation is carried out by methods well known in the art.
  • phosphatidylcholine and cholesterol are dissolved in ethanol at a 2:5:1 molar ratio. This solution is split into aliquots, and a range of concentrations of ursolic acid are added so that the loading capacity of liposomes can be determined.
  • One aliquot receives no ursolic acid to provide an empty liposome control.
  • Each aliquot is injected through a 30G1/2 needle into an equal volume of cold 1X phosphate-buffered saline (PBS).
  • PBS cold 1X phosphate-buffered saline
  • Encapsulated liposomes are analyzed by high-performance thin-layer chromatography (HPTLC) to determine the concentration of ursolic acid incorporated into the liposomes.
  • Encapsulated liposomes may be obtained, for example, under the trade name Merospheres, from Barnet Products Corporation in Englewood Cliffs, NJ.
  • the final concentration of ursolic acid in the liposomes used is between 0.001% to 0.9%, preferably from 0.005% to 0.5% and most preferably from 0.01% to 0.1%.
  • the concentration of ursolic acid in the final composition is between 0.0001 to 0.1%, preferably from 0.0002 to 0.005%, and most preferably from 0.0002 to 0.0003%.
  • the inventive composition further comprises a tanning agent.
  • a tanning agent any tanning agent known to those skilled in the art are within the scope of this invention, preferably dihydroxyacetone (DHA) is used.
  • DHA is a known skin darkening agent.
  • the use of DHA for skin tanning purposes produces what may be perceived by some as an unnatural-looking sun tan. Further, DHA may take several hours to effect a color change in the skin.
  • the inventive combination of DHA with URA liposomes beneficially provides a more natural looking tan at a more rapid rate because it is believed that the penetrative effectiveness of URA liposomes provide a pathway for DHA to more readily penetrate the skin.
  • tanning agents including but not limited to isatin, alloxan, ninhydrin, glyceraldehyde, mesotartaric aldehyde, glutaraldehyde, erythrulose, pyrazoline-4,5-dione derivatives, and 4,4-dihydroxypyrazoline-5 and derivatives thereof may used as an alternative or in conjunction with DHA.
  • DHA is used in an amount of from 0.001 % to 10%, preferably from 0.01% to 5% and most preferably from 0.1% to 3%.
  • the DHA or tanning agent may alternatively be encapsulated in a liposome to enhance delivery of the DHA or tanning agent into the skin.
  • the method of encapsulation may be as described hereinabove, or by any other known means of encapsulation.
  • the preferred embodiment of the present invention may also contain a penetration enhancer to facilitate penetration of the composition comprising the combination of DHA and URA liposomes.
  • Suitable penetration enhancers include but are not limited to pentylene glycol, C12-15 Alkyl Benzoate, polysorbate-polyethylenesorbitan-monolaurate (Tween-20 ®), polyethylene glycol, ethoxydiglycol, dimethylsulfoxide, sodium lauryl sulfate, lecithin and mixtures thereof.
  • the penetration enhancer is preferably used in an amount of from 0.001% to 10%, preferably from 0.01% to 8%, and most preferably from 0.1% to 5% by weight of the composition.
  • the composition optionally further comprises a cosmetically acceptable vehicle that is suitable for topical application to skin, hair and/or nails.
  • Cosmetically acceptable vehicles are well known in the art and are selected based on the end use of the application.
  • vehicles of the present invention include, but are not limited to, those suitable for application to the skin.
  • Such vehicles are well known to those of ordinary skill in the art, and can include one or more compatible liquid or solid filler diluents or vehicles which are suitable for application to the skin.
  • the exact amount of vehicle will depend upon the level of any other optional ingredients that one of ordinary skill in the art would classify as distinct from the vehicle (e.g., other active components).
  • the compositions of the present invention preferably comprise from about 75% to about 99.99%, more preferably from about 85% to about 99.99%, and most preferably from about 93% to about 98%, by weight of the composition, of a vehicle.
  • compositions herein can be formulated in a number of ways, including but not limited to emulsions.
  • suitable emulsions include oil-in-water, water-in-oil, water-in-oil-in-water, oil-in-water-in-oil, and oil-in-water-in-silicone emulsions.
  • Preferred compositions comprise an oil-in-water emulsion.
  • compositions of the present invention can be formulated into a wide variety of product types, including creams, waxes, pastes, lotions, milks, mousses, gels, oils, tonics and sprays.
  • Preferred compositions are formulated into lotions, creams, gels, and sprays.
  • These product forms may be used for a number of applications, including but not limited to, hand and body lotions, facial moisturizers, topical analgesics and make-ups/cosmetics. Any additional components required to formulate such products vary with product type and can be routinely chosen by one skilled in the art.
  • the formulation also can comprise other components that may be chosen depending on the carrier and/or the intended use of the formulation. It should be noted that a person of ordinary skill in the art is capable of determining the amounts of additional components that would be suitable for each formulation through routine experimentation. Additional components include, but are not limited to antioxidants (such as BHT); chelating agents (such as disodium EDTA); emulsion stabilizers (such as carbomer); preservatives (such as methyl paraben); fragrances (such as pinene); flavoring agents (such as sorbitol); humectants (such as glycerine); waterproofing agents (such as PVP/Eicosene copolymer); water soluble film-formers (such as hydroxypropyl methylcellulose); oil-soluble film formers (such as hydrogenated C-9 Resin); moisturizing agents (such as cholesterol); cationic polymers (such as Polyquatenium 10); anionic polymers (such as xanthan gum); vitamins (such as tocopherol);
  • Preferred additional components in the present invention include bronzers or other colorants that provide either an immediate tanned look, and/or provide the user with an indication of where the product has been applied so as to avoid streaking. Additionally preferred components include DHA-enhancing ingredients such as lactic acid, sugars, and film-forming agents.
  • compositions can also encompass one or more additional active components, and as such can be either cosmetic or pharmaceutical compositions in addition to tanning and concentrations may be determined by one skilled in the art to determine effectiveness of product as discussed in the present invention.
  • useful actives include, but are not limited to, those that improve or eradicate age spots, keratoses and wrinkles, analgesics, anesthetics, anti-acne agents, antibacterials, antiyeast agents, antifungal agents, antiviral agents, antidandruff agents, antidermatitis agents, antipruritic agents, antiemetics, antihyperkeratolytic agents, anti-dry skin agents, antiperspirants, antipsoriatic agents, antiseborrheic agents, antiaging agents, antiwrinkle agents, antiasthmatic agents and bronchodilators, antihistamine agents, wound-healing agents, vitamins, corticosteroids, additional tanning agents or hormones.
  • useful active agents include retinoids such as retinol, and esters, acids, and aldehydes thereof; ascorbic acid, and esters and metal salts thereof, tocopherol and esters and amide derivatives thereof; shark cartilage; milk proteins; alpha- or beta-hydroxy acids; DHEA and derivatives thereof; topical cardiovascular agents; clotrimazole, ketoconazole, miconozole, griseofulvin, hydroxyzine, diphenhydramine, pramoxine, lidocaine, procaine, mepivacaine, monobenzone, erythromycin, tetracycline, clindamycin, meclocyline, hydroquinone, minocycline, naproxen, ibuprofen, theophylline, cromolyn, albuterol, hydrocortisone, hydrocortisone 21-acetate, hydrocortisone 17-valerate, hydrocortisone 17-butyrate, betamethasone valerate
  • Particularly preferred embodiments of the present formulations are skin care lotions or creams used as a self-tanning product.
  • the present formulations may therefore be combined with additional aesthetic agents such as moisturizers, emollients or humectants.
  • additional aesthetic agents such as moisturizers, emollients or humectants.
  • useful combinations are oils, fats, waxes, esters, fatty acid alcohols, fatty acid ethoxylates, glycols, sugars, hyaluronic acid and hyaluronates, dimethicone, cyclomethicone, and the like. Further examples can be found in the International Cosmetic Ingredient Dictionary, CTFA, Ninth Edition, 2003 .
  • compositions are particularly useful as products useful as methods of tanning the skin through the inventive combination of DHA and URA liposomes.
  • Such methods comprise administering or topically applying to the skin a safe and effective amount of the composition of the present invention.
  • the amounts of the components in the compositions will vary depending upon the level of tanning desired and the individual's skin type.
  • a preferred method of cosmetically or pharmaceutically treating the skin is via topical application of a safe and effective amount of the novel composition to obtain the desired amount of tanning of the skin.
  • the amount of the composition and the frequency of topical application to the skin can vary widely, depending upon the individual's desired amount of tanning for total coverage or on an as-needed basis.
  • the method of the present invention is suitable for daily use.
  • topical application range from about once per month to about once daily, preferably from about once every three weeks to about once every two weeks, most preferably about once per week.
  • the composition is applied in an amount of from about 0.5 ml to 5 mg/cm 2 preferably 2 mg/cm 2 of skin.
  • the panel is divided into four groups of 7-8 corresponding to the four DHA materials.
  • the panelists apply the "control" formulation containing the nanoemulsion on the right arm and the assigned DHA material on the other arm.
  • exact amounts (800 ⁇ l each) of the test materials are dispensed on the forearms and blended in by the panelists. Color measurements are obtained with the Chromameter before treatment and after 30 minutes, 1 hour, 2 hour, 4 hours and 24 hours.
  • Red values ( ⁇ a*) are plotted against yellow coloration ( ⁇ b* values) within the "Natural Universe of Color” which exhibits the range of coloration from a suntan.
  • Formulation 5 containing both the Merospheres and Hydrolite ® -5 exhibits an early onset of tan which increases considerably in four hours. Formulation 5 exhibits the darkest tan at the 4 hour time point after which there is a slight reduction in the tan at the 24 hour time point.
  • Figures 2 and 3 show the tonality of the tested formulations at the 24 hour time point plotted in the Natural Universe of Tan and color.
  • This Universe represents the tonality of a suntan.
  • the tonality of all the formulations are within the Natural Universe of Tan ( Figure 2 ).
  • Further observation of color in the Natural Universe of Color ( Figure 3 ) shows that although all formulations are within this natural universe, the skin color falls more in the red coloration than observed historically for sunless tanning.
  • the panel is divided in three groups of 7-8 corresponding to the first three test materials.
  • the panelists apply the "control" Formulation 4 containing 3% DHA and no merospheres on the right arm and the assigned test material on the other arm.
  • exact amounts (800 ⁇ l each) of the test materials are dispensed on the forearms and blended in by the panelists.
  • Red values ( ⁇ a*) are plotted against yellow coloration ( ⁇ b* values) within the "Natural Universe of Color” which exhibits the range of coloration from a suntan.
  • Figures 5 and 6 exhibit the tonality of the formulations at the 24 hour time point plotted in the Natural Universe of Tan and Color. This universe represents the tonality of a suntan. The tonality of all the formulations are within the Natural Universe of Tan ( Figure 5 ). Further observation of color in the Natural Universe of Color ( Figure 6 ) shows that although all formulations are within this natural universe, the DHA formulation containing the cholesterol derived merospheres exhibit the strongest color.
  • the panel is divided in seven groups of 7-8 corresponding to the seven test materials.
  • the panelists apply the "control" formulation containing 3% DHA-PG on the right arm and the assigned test material on the other arm.
  • exact amounts (800 ⁇ l each) of the test materials are dispensed on the forearms and blended in by the panelists. Color measurements are obtained with the Chromameter before treatment and 5 hours and 24 hours.
  • Figures 8 and 9 depict the tonality of the formulations at the 24 hour time point plotted in the Natural Universe of Tan and Color. This universe represents the tonality of a suntan. The tonality of all the tested formulations are within the Natural Universe of Tan ( Figure 8 ).

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Claims (14)

  1. Une composition à usage topique pour l'auto-bronzage de la peau, comprenant
    de l'acide ursolique encapsulé dans un liposome
    un agent-auto-bronzant ; et
    un support acceptable du point de vue cosmétique
  2. La composition selon la revendication 1, laquelle l'acide ursolique est présent dans le liposome en proportion comprise entré 0,001% et 0,9% du poids de liposome.
  3. La composition selon la revendication 1, dans laquelle l'agent auto-bronzant est la dihydroxyacétone et est encapsulé dans un liposome.
  4. La composition selon la revendication 1, comprenant en outre un agent favorisant la pénétration choisi dans le groupe comprenant le benzoate d'alkyl en C12-15, le pentylène glycol, le polyéthylène glycol, l'éthoxydiglycol, le diméthylsulfoxyde, le lauryl sulfate de sodium, le monolaurate de polysorbate-potyéthylènesorbitan, la lécithine et des mélanges d'entre eux.
  5. La composition selon la revendication 1, comprenant en outre du pentylène glycol.
  6. Un procédé pour l'auto-bronzage de la peau comprenant l'application à la peau d' une composition comprenant de l'acide ursolique encapsulé dans un liposome, de la dihydroxyacétone, et un support acceptable du point de vue cosmétique
  7. Un procédé selon la revendication 6, dans lequel l'acide ursolique est présent dans le liposome en une proportion comprise entre 0,001% et 0,9%) du poids de liposome
  8. Un procédé selon la revendication 6, dans lequel la dihydroxyacétone est encapsulée dans un liposome.
  9. Un procédé selon la revendication 6, dans lequel la composition comprend en outre un agent favorisant la pénétration choisi dans le groupe comprenant le benzoate d'alkyl en C12-15, le pentylène glycol, le polyéthylène glycol, l'éthoxydiglycol, le diméthylsulfoxyde, le lauryl sulfate de sodium, le monolaurate de polysorbate-poly-éthylènesorbitan, la lécithine et des mélanges d'entre eux.
  10. Un procédé selon la revendication 6, comprenant en outre du pentylène glycol.
  11. Un procédé pour bronzer la peau comprenant l'application à la peau d'une composition comprenant de l'acide ursolique encapsulé dans un liposome, de la dihydroxyacétone encapsulée dans un liposome et une support acceptable du point de vue cosmétique.
  12. Un procédé selon la revendication 11, dans lequel l'acide ursolique est présent dans le liposome en une proportion comprise entré 0,001% et 0,9% du poids de liposome.
  13. Un procédé selon la revendication 11, dans lequel la composition comprend en outre un agent favorisant la pénétration choisi dans le groupe comprenant le benzoate d'alkyl en C12-15, le pentylène glycol, le polyéthyléne glycol, l'éthoxy-diglycol, le diméthylsulfoxyde, le lauryl sulfate de sodium, le monolaurate de polysorbate-polyéthylènesorbitan, la lécithine et des mélanges d'entre eux
  14. Un procédé selon la revendication 11, comprenant en outre du pentylène glycol.
EP05772127.6A 2004-07-01 2005-06-27 Compositions cosmetiques et procede a base d'un agent bronzant et d'acide ursolique encapsule dans un liposome Not-in-force EP1765463B1 (fr)

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US58474904P 2004-07-01 2004-07-01
PCT/US2005/022650 WO2006007487A2 (fr) 2004-07-01 2005-06-27 Compositions cosmetiques et procede a base d'un agent bronzant et d'acide ursolique encapsule dans un liposome

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EP1765463A2 EP1765463A2 (fr) 2007-03-28
EP1765463A4 EP1765463A4 (fr) 2010-11-03
EP1765463B1 true EP1765463B1 (fr) 2014-07-30

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US (1) US7794694B2 (fr)
EP (1) EP1765463B1 (fr)
JP (1) JP4589386B2 (fr)
AU (1) AU2005262369B2 (fr)
CA (1) CA2571796C (fr)
ES (1) ES2511490T3 (fr)
WO (1) WO2006007487A2 (fr)

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CN102892412B (zh) 2010-03-12 2015-09-30 博格制药有限责任公司 辅酶Q10(CoQ10)的静脉内制剂及其使用方法
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AU2005262369B2 (en) 2008-08-28
EP1765463A2 (fr) 2007-03-28
CA2571796C (fr) 2009-06-02
WO2006007487A3 (fr) 2006-08-17
CA2571796A1 (fr) 2006-01-19
WO2006007487A2 (fr) 2006-01-19
EP1765463A4 (fr) 2010-11-03
AU2005262369A1 (en) 2006-01-19
US20060002870A1 (en) 2006-01-05
US7794694B2 (en) 2010-09-14
JP4589386B2 (ja) 2010-12-01
ES2511490T3 (es) 2014-10-22
JP2008505081A (ja) 2008-02-21

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